1. Field of the Invention
This invention relates to new hydroxy-containing alkyl-substituted bicycloalkane ether compositions, and particularly hydroxy-containing ethers of akyl-substituted norbornanes, which are suited for use in making valuable detergent and lubricating compositions, and to an efficient process for preparing the said compositions from substituted norbornenes.
The invention specifically provides new hydroxy-containing alkyl-substituted bicycloalkane ether compositions represented by the formula ##STR1## wherein R.sub.1 is hydrogen or methyl, R.sub.2 is a substantially linear alkyl group preferably containing from 4 to 26 carbon atoms, and A is a divalent hydrocarbon radical which preferably is a linear or branched radical containing from 2 to 12 carbon atoms.
The new compositions of the present invention possess a variety of valuable properties which make them suitable for use in many commercial applications, such as in the preparation of surface active agents, detergent compositions, lubricating compositions and the like. The new products are particularly useful in the preparation of detergent compositions, such as by reaction through the hydroxyl group with ethylene oxide, to form valuable polyoxyethylene derivatives. These products being free of alkylphenol groups are thus more biologically degradable and useful in the preparation of laundry or other cleaning products which are ultimately discharged into the sewer and readily attacked by bacterial agents.
2. Prior Art
Some biologically degradable detergent compositions, such as those described in U.S. Pat. No. 3,370,080 have been prepared by forming a norbornane alcohol by hydration of norbornene and then reacting the secondary alcohol with ethylene oxide. However, the products of the present invention represent a valuable improvement in that they give narrower and better regulated molecular weight distribution than obtainable by the alkoxylation of the secondary hydroxyl group of the prior known products.
Further advantage is also found in the fact that the new compositions can be prepared from inexpensive compounds, such as alpha-olefins and cyclic dienes, and obtained in high yields by a simple two-step process; thus presented an economic advantage over many of the known biologically degradable detergent compositions.